Head of Operations- Miami, Florida

The Calendar Group

$150K — $175K *
Miami, FL 33186In-Person
Media
8 - 10 years of experience
Job Overview by Ladders

Qualifications

  • 8+ years of experience in operations, business management, or organizational leadership.
  • Proven track record of building teams, systems, and processes in entrepreneurial or high-growth settings.
  • Strong leadership skills in team management, recruiting, and organizational development.
  • Experience in budget management and collaboration with finance, accounting, and legal partners.
  • Ability to translate abstract ideas into structured plans and measurable outcomes.
  • Preferred background in media, entertainment, digital content, or startup environments.
  • Must be based in Miami and open to occasional travel.

Responsibilities

  • Serve as a primary execution partner to the Founder and manage day-to-day operations.
  • Develop structured plans, timelines, and deliverables based on the Founder's vision.
  • Build scalable systems and workflows, including SOPs and reporting structures.
  • Establish organizational priorities and accountability across teams.
  • Define roles, responsibilities, KPIs, and reporting relationships to improve efficiency.
  • Lead recruiting, onboarding, and employee development to build a strong team.
  • Maintain operational oversight in content production and post-production processes.
  • Collaborate with internal teams and vendors to keep projects on schedule and within budget.
  • Identify new business opportunities that align with the Founder's vision and expand revenue streams.
  • Support financial operations, monitoring budgets, and enhancing cost efficiency.

Benefits

  • Opportunity to work closely with the Founder in a dynamic, fast-paced environment.
  • Hands-on leadership role within a lean organization offering significant impact and influence.
  • Chance to develop scalable systems and processes from the ground up.
  • Culture of ownership and communication fostered within a growing team.
  • Opportunities for professional development and team building.
  • Involvement in strategic decisions that influence the company's future trajectory.
Full Job Description
A media and entertainment brand is seeking a highly driven Head of Operations to serve as the Founder's operational right hand and help lead the company through its next stage of growth. This is a hands-on leadership role within a lean, founder-led organization. The successful candidate will take ownership of day-to-day operations, build and develop the team, establish scalable systems, create accountability, and ensure priorities move forward. The ideal candidate combines strong operational discipline with a startup mentality and is energized by building an organization.

Responsibilities
  • Serve as the Founder's operational right hand and primary execution partner.
  • Translate ideas and priorities into structured plans, timelines, and deliverables.
  • Build scalable systems, workflows, SOPs, reporting structures, and communication rhythms.
  • Establish clear priorities, ownership, timelines, and accountability across the organization.
  • Define roles, responsibilities, KPIs, and reporting relationships.
  • Identify hiring needs and lead recruiting, interviewing, onboarding, and employee development.
  • Manage and develop employees while creating a culture of ownership, communication, and follow-through.
  • Maintain operational visibility across content production and post-production.
  • Ensure projects are properly planned, staffed, budgeted, scheduled, and executed.
  • Collaborate with internal production teams and outside vendors to prevent delays and operational breakdowns.
  • Evaluate new business opportunities and turn Founder-led ideas into actionable plans.
  • Help expand and diversify revenue through partnerships, products, intellectual property, live experiences, and other ventures.
  • Partner with accounting, finance, legal, and other external advisers.
  • Establish and monitor company, departmental, and project budgets.
  • Support forecasting, financial reporting, and operating plans.
  • Review spending, identify opportunities to improve efficiency, and negotiate with vendors and partners when appropriate.
  • Reduce the Founder's involvement in day-to-day management so they can focus on content, creative direction, brand growth, and major opportunities.

Qualifications
  • 8+ years of experience in operations, business management, or organizational leadership.
  • Demonstrated success building teams, systems, and processes within a founder-led, entrepreneurial, or high-growth organization.
  • Strong experience in team leadership, recruiting, project management, and organizational development.
  • Experience managing budgets and working with finance, accounting, legal, and external partners.
  • Proven ability to turn loosely defined ideas into structured plans and measurable results.
  • Media, entertainment, digital content, creator economy, production, consumer brand, or startup experience strongly preferred.
  • Based in Miami and willing to travel occasionally.

Compensation: 150,000-175,000, depending on experience.

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